Inside Kanye West And Caitlyn Jenner's Relationship

On July 4, 2020, Kanye West announced he was running for president. Since then, he's made headlines, revealing he and wife Kim Kardashian had contemplated aborting their oldest daughter, North West, at his first presidential rally. He also took to Twitter to share that he had been trying to divorce his wife for years. 

Kim spoke out in a lengthy statement asking people for grace as her husband struggles with his mental health. In the midst of all that, TMZ cameras caught up with Kim's former stepfather, Caitlyn Jenner, in July 2020 with a paparazzo asking if she intended to vote for Kanye. Instead of answering that question, Caitlyn commented: "Well, I texted him and said, 'Can I be your VP," remarking, "What a combination." 

During an appearance on Good Morning Britain in August 2020, Caitlyn said (via People): "I made that as a joke about being his VP when he announced that." Still, she emphasized, "I hope for the best for him. He's a really good guy." 

At the time, Caitlyn revealed the two hadn't "had a chance" to chat since Kanye announced his plans to run. Even so, the former Olympian has a lot of praise for the rapper. "The only thing I can talk about is really how he treated me through everything and he has been the most kind, loving human being and so good to me throughout the years and especially going through everything I've been going through in the last five years," seemingly referencing her transition. 

Caitlyn described Kanye as "such a good friend," which is interesting given Caitlyn's strained relationship with ex-wife Kris Jenner and other members of the Kardashian family.

During her Good Morning Britain appearance, Caitlyn Jenner had this to say about Kanye West (via People): "He's a good person. He's got a big heart." She added, "He deals like everybody deals with things in their lives." When she was asked about Kanye's presidential aspirations, Caitlyn said she "can't even go there," remarking, "We're living in such a political environment today. It's like, I don't even want to discuss or talk about politics anymore." Overall, Caitlyn says Kanye is "extremely supportive" of her, which has always appeared to be the case.

During a 2015 episode of her short-lived reality show I Am Cait, Caitlyn said: "I love [Kanye's] open-mindedness and I love how he's helped Kim come to grips with what's going on." During that episode, Kanye told Caitlyn: "I think this is one of the strongest things that have happened in our, you know, existence as human beings that are so controlled by perception because you couldn't have been up against more."

He continued: "Like, your daughter's a supermodel, you're a celebrity, you have every type of thing, and it was still like 'f**k everybody this is who I am.'" During a 2015 interview for SHOW studio's "In Camera" series, Kanye had this to say: "I just feel so proud to be in a family that has so many people breaking ground for the generations to come ... I feel proud ... that I can be next to a wave of 'this is who I am.' And that is all I'm about."

In 2016, Kanye West featured naked likenesses of numerous celebrities in his "Famous" music video, which was a surprise to everyone except Kim Kardashian and Caitlyn Jenner, who the rapper notified ahead of time. During a 2016 Keeping Up With the Kardashians episode, Kris Jenner was livid about Caitlyn's appearance in the music video. 

In regards to the music video, Kris said (via Entertainment Tonight): "I was speechless watching it because I didn't know what I was going to be looking at." She added, "To see that up on the screen that big was kind of crazy." In that episode, Kris told Khloé Kardashian that she was "so pissed" about Kim styling Caitlyn for the ESPY Awards in addition to telling Kim: "you are a f**king traitor!" In a 2016 interview with Bill Simmons for his HBO show Any Given Wednesday, Caitlyn noted that she felt "honored" to appear in the music video.

According to People, in a 2017 KUWTK episode, Kim said Caitlyn was a "liar" for comments she made about Kim's father, Robert Kardashian Sr., in her autobiography, which caused major issues between Caitlyn, Kris, and the Kardashian women. That's why Kanye made headlines in 2018 when he shared a screenshot of his text conversations with Caitlyn, per Entertainment Tonight. They discussed his Yeezy fashion line, which Caitlyn is clearly a fan of since she wore Yeezy sneakers when she showed up to film I'm a Celebrity Get Me Out Of Here in 2019, according to The Sun. 

Even though Caitlyn Jenner seemingly has nothing but praise for Kanye West when it comes to their personal interactions, she isn't the biggest fan of his music, despite being in the "Famous" music video. It's not that she dislikes his catalog, she apparently just doesn't know any of the songs.

Cosmopolitan reported that Caitlyn was asked to sing some Kanye songs during a 2019 episode of I'm a Celebrity Get Me Out Of Here, but she couldn't come through on the request, admitting, "Unfortunately I don't know any Kanye West songs," before joking, "I'm going to get into so much trouble when I get home!" During another episode, Caitlyn said: "Kanye is a good friend of mine and he's good to have an intelligent and interesting conversation with," according to The Sun. 

With time, Kim Kardashian and Caitlyn seemed to patch things up, celebrating Caitlyn's birthday together in October 2019. Kim, Kanye, Caitlyn, and Caitlyn's best friend, Sophia Hutchins, attended an Academy Awards after party in February 2020, with Caitlyn posting: "Love partying with family!"

Both Kanye and Caitlyn have had very public ups and downs with members of their famous family, but never with each other. In contrast, their relationship has seemingly been full of acceptance and support.